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Preparation method of 6-substituted phenanthridine compound

A compound, phenanthridine technology, applied in the field of preparation of organic compounds, can solve the problems of expensive nickel catalysts, harsh reaction conditions, long reaction time, etc., and achieves the effects of strong substrate universality, readily available raw materials, and simple operation.

Inactive Publication Date: 2018-03-13
ZHEJIANG UNIV OF TECH
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Problems solved by technology

[0003] At present, the synthetic method of relevant 6-substituted phenanthridines reported at home and abroad mainly contains the following several methods: (1) take aryl trifluoromethanesulfonate and N-trimethylsilyl imine as raw material in palladium catalyst catalysis The following synthesis (see Org.Lett.2011,13,1486), this method uses transition metal catalyzed cyclization imine method, which uses expensive noble metal catalysts and needs to add toxic organophosphorus compounds as ligands, and the conditions are relatively harsh By-products; (2) One-pot synthesis of aryne intermediates through diazobenzene-2-carboxylate ethyl ester, aniline and aromatic aldehyde as raw materials (see J.Org.Chem.2006,71,9241-9243), This method is only suitable for the synthesis of specific phenanthridine compounds, which limits the expansion of substrates; (3) with alkynes and nitriles as raw materials, synthesized by [2+2+2] cycloaddition (see Chem.Commun. 2008,2992.), the nickel catalyst used in this method is expensive and has a long reaction time; (4) using isocyanate as a raw material, it is synthesized by catalyzing aza-Wittig cyclization (referring to Org.Lett.2008,10,2589), this The method uses the toxic organic phosphorus-containing compound cyclophosphene oxide and the method limits the substrate expansion; (5) using the cyclic ketone of O-phenylalanine and related derivatives as raw materials, synthesized by hydrothermal reaction ( See Org.Lett.2003,5,1605.), the required reaction temperature of this method is extremely high (greater than 200 degrees Celsius), and the reaction conditions are harsh

Method used

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  • Preparation method of 6-substituted phenanthridine compound
  • Preparation method of 6-substituted phenanthridine compound
  • Preparation method of 6-substituted phenanthridine compound

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0024]

[0025] Add 119.7mg (0.3mmol) N-[1-phenyl-1'-biphenyl]benzenesulfonamide, 212.6mg (0.6mmol) Selectfluor and 2.4mg (0.03mmol) Se into a 25mL thick-walled pressure-resistant tube, Acetonitrile was used as a solvent, and the dosage was 3 mL. Next, it was magnetically stirred at 60° C. for 12 hours. Then, transfer the reaction solution to a 25mL separatory funnel and add 8mL of dichloromethane and 8mL of water to extract simultaneously, extract 3 times, get the organic layer containing dichloromethane and target product each time, i.e. the extract, and in the last Add 239.4 mg of column chromatography silica gel (100-200 mesh) to the extract, remove the solvent by distillation under reduced pressure (vacuum degree is 0.08kPa), and separate the residue by column chromatography. The volume ratio of petroleum ether and ethyl acetate is 10 : The mixed solution of 1 was eluted as the eluent, and the eluate containing the target product was collected, and the solvent was eva...

Embodiment 2

[0028]

[0029] With 136.5g (0.3mmol) N-[1-phenyl-1 '-biphenyl (4'-tert-butyl)] benzenesulfonamide, 204.4mg (0.9mmol) DDQ and 3.4mg (0.03mmol) SeO 2Add it to a 25mL thick-walled pressure-resistant tube, use DMF as a solvent, and use 1mL. Next, it was magnetically stirred at 100° C. for 24 hours. Then, transfer the reaction solution to a 25mL separatory funnel and add 6mL ethyl acetate and 8mL water to extract simultaneously, extract 3 times, get the organic layer containing ethyl acetate and the target product each time, i.e. the extract, and in the last Add 273 mg of column chromatography silica gel (100-200 mesh) to the extract, remove the solvent by distillation under reduced pressure (vacuum degree is 0.08kPa), and separate the residue by column chromatography. The volume ratio of petroleum ether and ethyl acetate is 10: The mixed solution of 1 was eluted as an eluent, and the eluate containing the target product was collected, and the solvent was evaporated to obtain ...

Embodiment 3

[0032]

[0033] Add 129.9 mg (0.3 mmol) N-[1-phenyl-1'-biphenyl(4'-chloro)]benzenesulfonamide, 737.7 mg (1.2 mmol) Oxone and 4.7 mg (0.06 mmol) Se to a 25 mL thick In the wall pressure tube, 1,4-dioxane was used as a solvent, and the dosage was 3mL. Next, magnetic stirring was performed at 110° C. for 36 hours. Then, transfer the reaction solution to a 25mL separatory funnel and add 15mL of dichloromethane and 8mL of water to extract at the same time, extract 3 times, each time get the organic layer containing dichloromethane and target product, i.e. the extract, and in the last Add 259.8 mg of column chromatography silica gel (100-200 mesh) to the extract, remove the solvent by distillation under reduced pressure (vacuum degree is 0.08kPa), and separate the residue by column chromatography. The volume ratio of petroleum ether to ethyl acetate is 10 : The mixed solution of 1 was eluted as eluent, and the eluate containing the target product was collected, and the solvent w...

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Abstract

The invention discloses a preparation method of a 6-substituted phenanthridine compound represented by a formula (I), wherein a N-[1-phenyl-1'-biphenyl]benzenesulfonamide compound represented by a formula (II) is used as a raw materials and is subjected to a reaction in an organic solvent under the action of a [Se] / Selectfluor catalyst to prepare a corresponding target product represented by the formula (I). According to the present invention, the synthesis method has advantages of low harm on environment, relatively mild reaction conditions, energy consumption reducing, high product selectivity, easy operation and the like. The formulas (I) and (II) are defined in the specification.

Description

(1) Technical field [0001] The invention relates to a preparation method of an organic compound, in particular to a preparation method of a 6-substituted phenanthridine compound. (2) Background technology [0002] Phenanthridine is an essential core structure in many natural products and other important molecules. It has a wide range of biological activities and applications, including antibacterial, antiprotozoal and anticancer. Among them, Ethidium, a member of the famous phenanthridine class, is a common and versatile DNA / RNA intercalator, so that the development of efficient and easy-to-obtain synthetic methods for phenanthridine derivatives has aroused widespread interest among chemists. Therefore, the research and development of related synthesis technologies of phenanthridine derivatives 6-substituted phenanthridine have broad application prospects. [0003] At present, the synthetic method of relevant 6-substituted phenanthridines reported at home and abroad mainly ...

Claims

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Application Information

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IPC IPC(8): C07D221/12
CPCC07D221/12
Inventor 刘运奎施冬冬徐峥
Owner ZHEJIANG UNIV OF TECH
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